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Crazy Good Turns

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Now displaying: April, 2026
Apr 3, 2026

Bill Gurley is a venture capitalist known for early investments in Uber, Grubhub, Zillow and many others. Gurley joins us to discuss “Running Down a Dream,” his new book — which is full of career advice that is as surprising as it is useful. 

In this episode, we discuss:

  • The Power of Mentorship: Why Bill feels a moral urge to share what he's learned with the world.

  • The "Safe" Path Trap: Why the jobs your parents think are safe might actually be the most dangerous in the age of AI.

  • The Peer Group Secret: Why sharing your best ideas with others actually makes you more successful than hoarding them.

  • Finding Your Obsession: Why Bill looks for "fascination" rather than just "passion."

 

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